Melanotan-1

Base Information

• Chemical Name: Melanotan-1
• CAS No.: 75921-69-6
• Molecular Formula: C78H111N21O19
• Molecular Weight: 1646.87
• Mol file: 75921-69-6.mol

Synonyms:alpha-Msh, nle(4)-phe(7)-;alpha-Msh, norleucyl(4)-D-phenylalanyl(7)-;(Nle4,D-Phe7)-alpha-MSH;Afamelanotide;Msh, 4-norleucyl-7-phenylalanine-alpha-;(Nle4-D-Phe7)-alpha-Melanocyte-stimulating hormone;alpha-Melanotropin, 4-L-norleucine-7-D-phenylalanine-;

Chemical Property of Melanotan-1

Chemical Property:

• Refractive Index: 1.674
• PKA: 4.43±0.10(Predicted)
• PSA: 642.98000
• Density: 1.46 g/cm³
• LogP: 3.12050
• Storage Temp.: −20°C

Purity/Quality:

99%, ^*data from raw suppliers

[Nle4,D-Phe7]-α-MSH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: [Nle4, D-Phe7]-α-Melanocyte Stimulating Hormone trifluoroacetate salt has been used to detect its effect on O2 consumption and CO2 production in C57BL/6 mice.1It is also used to determine its effect on leptin secretion in the primary cultures of differentiated adipocytes.

Technology Process of Melanotan-1

There total 1 articles about Melanotan-1 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Val-OH (68858-20-8) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0,136083-74-4,121343-82-6) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + Fmoc-Lys-OH (105047-45-8) + Fmoc-D-Phe-OH (86123-10-6) + Fmoc-His(Trt)-OH (109425-51-6) + Fmoc-(S)-2-aminohexanoic acid (77284-32-3,144701-20-2) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → NDP-MSH (75921-69-6)

Guidance literature:

Fmoc-Val-OH; With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 0.5h;

With piperidine; In N,N-dimethyl-formamide; for 0.333333h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid; Fmoc-Tyr(tBu)-OH; Fmoc-Lys-OH; Fmoc-D-Phe-OH; Fmoc-His(Trt)-OH; Fmoc-(S)-2-aminohexanoic acid; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

DOI:10.1021/acs.jmedchem.7b01295

Reference yield:

NDP-MSH (75921-69-6) + [125I]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate → [125I][Nle4, D-Phe7, FIB-Lys11]α-MSH

Guidance literature:

With borate buffer; In acetonitrile; at 45 ℃; for 0.5h; pH=8;

DOI:10.1021/ml500423v

Reference yield:

NDP-MSH (75921-69-6) + [18F]2,3,5,6-tetrafluorophenyl 4-fluoro-3-iodobenzoate → [18F][Nle4, D-Phe7, FIB-Lys11]α-MSH

Guidance literature:

With borate buffer; In acetonitrile; at 50 ℃; for 0.166667h; pH=8;

DOI:10.1021/ml500423v

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Val-OH

Fmoc-Pro-OH

Fmoc-Ser(tBu)-OH

Refernces